Top Chicago Water Tours - page 2

Spectacular Lake Michigan/Skyline Fireworks Party Cruise

1 hour 15 minutes

(2)

from $44

Explore the Chicago River in a unique way with this 120-minute Guided Ghost Tour. Learn about the city's haunted history, including the Great Chicago Fire and the Eastland Disaster. You are welcome to bring your own beverages and food/snacks to fully enjoy your time on the water. Departing from the Chicago Riverwalk, this is a fun and engaging way to experience the spooky side of the city. This tour is typically smaller allowing for you to interact with the tour guide! Ask all the questions, we are ready! - 120-minute ghost tour on the Chicago River for up to 18 passengers - Fun bring-your-own beverage/snacks experience with a u-shaped bar and coolers - Learn about Chicago's haunted history and significant events - Departures from the Chicago Riverwalk—15-minute early arrival required to allow time for check in and depart on time.

Chicago River Guided Ghost Tour

Admire up-close views of the Chicago skyline—and a fireworks show over the city—on this tiki bar boat tour. In the evening, make your own way to the departure point at the Chicago Riverwalk, hop aboard, and get comfortable in the air-conditioned seating area or on the deck. Purchase cocktails and food from the on-site tiki bar, watch the city float by, and then sit back and take in the show.

(6)

from $65

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the spectacular fireworks display at Navy Pier. This 1.5-hour cruise offers a unique perspective of the city while providing a relaxed atmosphere for friends and family to gather and enjoy the show. Boarding begins 15 minutes prior to departure, so arrive early to secure your spot and make the most of this dazzling experience. - 1.5-hour cruise featuring panoramic views of Chicago's skyline - Marvel at the iconic fireworks show off Navy Pier - Departing and returning to 111 N Lake Shore Drive

(34)

from $52

Chicago Fireboat Fireworks Cruise

1 hour 30 minutesFree Cancellation

4.7

(15)

from $57

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

1 hour 15 minutes

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

(126)

from $42

Chicago's Fireworks Show aboard Tall Ship Windy!

Chicago's Fireworks Show aboard Tall Ship Windy!

Chicago River Floating Tiki Bar Cruise Friday and Saturday

4.7

(24)

from $114

1 hour 15 minutes

4.7

(17)

from $42

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Chicago 3D Fireworks Cruise

3.9

(32)

from $105

See Chicago's magnificent skyline at night!

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

4.2

(264)

from $52

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

4.3

(31)

from $42

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

(379)

from $63

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Enjoy a fun, festive, and one-of-a-kind way to admire the Chicago skyline and views over Lake Michigan aboard this tiki boat tour. Choose from several start times, meet your tiki-themed vessel right on the Chicago Riverwalk, and climb aboard. As you sail along the Chicago River and out onto Lake Michigan, you’ll enjoy a new perspective on the Windy City—and can purchase mimosas and other beverages at the on-board cash bar.

3.9

(35)

from $42

Chicago Lake Michigan Skyline Sunday Funday Party Cruise

Chicago Lake Michigan Skyline Sunday Funday Party Cruise

1 minute to 1 hour 30 minutes

4.4

(9)

from $42

Monday Night Concert Series: Blues and Views Aboard Tall Ship

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

Monday Night Concert Series: Blues and Views Aboard Tall Ship

2 hours

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

(1)

from $81

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

3.7

(9)

from $101

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of Washington DC’s iconic landmarks, DJ entertainment, and festive décor. Our team will happily take care of the details, leaving you to celebrate the holidays on the Potomac River with your friends and family. Happy Holidays Includes Three-hour Christmas Eve dinner cruise on the Potomac River Chef-prepared, three-course, plated holiday menu The most breathtaking views of the nation's greatest landmarks including the Washington Monument and Lincoln Memorial DJ entertainment Complimentary coffee, hot tea, and iced tea

4.3

(43)

from $74

Christmas Eve Plated Dinner Cruise on Lake Michigan

Christmas Eve Plated Dinner Cruise on Lake Michigan

3 hoursFree Cancellation

from $198

Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!

Chicago River Cycleboat Cruise

1 hour 30 minutesFree Cancellation

(13)

from $65

Discover the fascinating history of Chicago from a whole new perspective — on the water! This 120-minute Guided History Tour along the Chicago River brings the city’s past to life through captivating stories, iconic landmarks, and little-known facts that shaped the Windy City into what it is today. • Chicago’s transformation from swamp land to industrial hub to the modern metropolis it is today • The dramatic story of the Great Chicago Fire of 1871 and how the city rebuilt stronger than ever • Tales of Chicago’s most infamous gangsters and Prohibition-era legends • The groundbreaking 1893 World’s Fair and the inventions it introduced to the world • The incredible reversal of the Chicago River — its purpose and lasting impact on the city’s future Step aboard and experience how history, architecture, and innovation flow together on this unforgettable journey through Chicago’s past and present.

BYOB Chicago River Guided History Tour

(4)

from $65

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

Heading out to Four Mile Crib on a beautiful day of sailing.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Step aboard the iconic Cap Streeter for an unforgettable evening cruise departing from Navy Pier. Shoreline’s Special Event Series combines curated local beverage tastings, delicious light bites, music, and breathtaking skyline views into one elevated Chicago experience. Whether you’re planning a date night, gathering with friends, or simply looking to unwind after work, this 90-minute cruise offers the perfect blend of relaxation, entertainment, and local flavor on the water. 2026 Special Event Lineup Brew Cruise with Revolution Brewing Date: July 9 Cider Cruise with Right Bee Cider Date: July 23 Brew Cruise with Haymarket Brewery Date: August 13 Tiki Luau with Three Dots and a Dash Date: August 27 Wine Tasting with Lynfred Winery Date: September 10 Boarding 7-7:30PM Cruise 7:30-9:00PM

(73)

from $508

Per group

Happy Hour Cruises on Lake Michigan 21+

1 hour 30 minutesFree Cancellation

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. Your private tour ensures a more personal experience. If you would like to take the tour at a time other than what is offered, please note in special requests field when booking. The best way to tour at this time! Sanitized vehicles with just your group.

from $62

Private Chicago City Minibus Tour

Historical and Architectural Chicago Fireboat River & Lake Cruise

(1)

from $999

Per group

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Top Attractions in Chicago

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What are people saying about Chicago

Ian_M, Jul 2026

Very informative and enjoyable tour

A very good tour, offering great value, and to travel on a fireboat made it more relevant. The guide was informative and funny too. Nice to stsrt outsifmde the city, trip around the harbour and go through the lock gates. Good information on architecture and buildings. A trip out to the lighthouse toward the end of tour was also an added bonus.

Chicago Sightseeing River and Lake Cruise

Victoria_G, Jul 2026

Best of both worlds

The best of both cruising worlds - Chicago river and the lake cruise in one! Hear about the architecture on the banks of Chicago River then go through the engineering marvel of Great Lock and end up on Lake Michigan, where the views of skyline 🏙️ are unmatched! Totally recommend

Chicago By Night River and Lake Cruise

Lisa_G, Jul 2026

Very informative and beautiful

Taking the sunset architectural cruise near the Riverwalk was easily one of the highlights of our trip. Seeing the city's iconic skyline transition from the golden hour glow into the beautifully lit evening cityscape is an absolute must-do. The vessel was comfortable, the atmosphere was relaxed, and the tour provided fascinating insights into the history and design behind Chicago's world-famous buildings. If you want a peaceful, breathtaking, and informative way to experience the city from the water, this is it! Highly recommended.

Chicago's Fireworks Show aboard Tall Ship Windy!

Chris_T, Jul 2026

A great trip aboard the...

A great trip aboard the tall ship Windy. The fireworks display was well worth waiting for and highly recommended! And afterwards I was one of the 4 volunteers who helped raise the mast (quite an enjoyable experience) for us to sail around before returning. The crew were very accommodating. Altogether a quite relaxing time really.

Small-Group Sightseeing Boat Tour in Chicago

Matthew_K, Jul 2026

Outstanding Experience with Captain Ken & Ryan

Captain Ken and Ryan were fantastic! They were friendly, professional, and incredibly experienced. Captain Ken's knowledge of Chicago, its architecture, history, and the waterways was truly impressive, and he shared it in a way that was engaging, entertaining, and easy to follow. Our family of four took the evening cruise departing around 6:35 p.m., and it ended up being the highlight of our entire Chicago trip. Cruising across Lake Michigan before entering the Chicago River offered breathtaking views of the skyline, and the combination of beautiful scenery, fascinating history, and entertaining narration made for an unforgettable experience. If you're looking for a tour that's both relaxing and informative, this is it. We would absolutely book again and highly recommend it to anyone visiting Chicago. It's worth every penny!

Chicago CityPASS®

Paul_M, Jun 2026

Save some cash with the CityPass

City Pass is a great way to see Chicago if you know you are going to some of the most popular museums (Field and Shedd) and then allow for some other excursions that you wouldn’t necessarily want to pay full price for (Skydeck, Architecture Cruise) but were still enjoyable and save some cash overall. The Adler Planetarium was a nice find. I would not use for the art institute if you have kids under 13 as they get in for free.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Amena_S, Apr 2026

Top tier experience

It was amazing from start to finish. Very aesthetically pleasing and service and food was top tier. Our server Heather was a perfect 10 across the board. Her recommendations, her spirit, her genuine energy was a breath of fresh air. She helped us with food selections, which were amazing down to photo opportunities. She even led us to the amazing bartender Keisha who made the best bottomless mimosas to say the least. We had to stop by the bar to let Ms Keisha know how well she mixed those cocktails. This was truly an amazing birthday brunch experience. Great way to start my birthday!!!

Chicago City Tour with Architecture River Cruise Option

Marty_R, Mar 2026

Wonderful tour with Alan!

Alan was a great tour guide - lots of fun information and entertained all of our questions. It was my 17 year old daughter’s first trip to Chicago, so I wanted her to get to see as much of the main parts of the city as possible, and we definitely hit all the ones I had on my list! The bus itself was clean and well cared for, and I like that it was smaller than the other buses because it made it much more personal. Alan also had great recommendations for places to go, where to eat, and was able to give ideas for spots that were of interest to us specifically. Highly recommended!

Chicago Seadog River & Lake Architectural Tour

Steve_S, Sep 2025

Ryan and his entire team...

Ryan and his entire team were fantastic. They provided fun and engaging tour also allowing time for questions. We highly recommend attending this tour. It is suitable for all ages and especially fun for those who are interested in learning about the architecture of the downtown area.